


The Riddler Dates a Henchman

by d2fmeasurement



Category: Gotham - Fandom, Powerless - Fandom
Genre: M/M
Language: English
Status: Completed
Published: 2017-02-26
Updated: 2017-02-26
Packaged: 2018-09-27 00:24:06
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,494
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9940706
Author URL: https://archiveofourown.org/users/d2fmeasurement/pseuds/d2fmeasurement
Summary: Crossover between Powerless and Gotham. Reggie starts banging his boss. Takes place a few years after the events of Gotham.





	

Reggie had been working as a henchman for a couple months. He still hadn’t died, which was very exciting. 

Today while he and the others were waiting for their share of today’s haul, the Riddler himself walked out to supervise. Reggie kept glancing over at him, but tried not to look intimidated. He took his money from the middleman, then turned to leave.

But, suddenly Edward declared, “You there. With the traditionally handsome features.”

Reggie looked over at him, then wondered if that was conceited.

“Yes, you,” he said. “Come here.” He snapped his fingers impatiently.

Reggie walked over to him. “Yes?” He quickly added, “Sir?”

“I need to speak to you privately,” he said. Reggie nervously followed Edward into his office. 

“Am I in trouble? I swear I haven’t taken extra money or betrayed you in any way or anything like that,” he said.

Edward slowly smiled. “You’re so scared,” he said.

“Yeah, but I didn’t do anything wrong. I swear. You have to believe me,” Reggie said.

Edward put his hand on Reggie’s chest so he could feel his heart race, then slowly moved his hand to feel his bicep. “You seem like you can take care of yourself,” he said.

“Sure, in a normal fight,” Reggie said. “But… you’re The Riddler.”

Edward grinned. “Yes, I am.” He watched Reggie cower a little longer, then said, “You’re not in trouble.”

Reggie let out a breath. “Oh thank God,” he said.

“I can be a page on your calendar or a fruit on the palm,” Edward said. “What am I?”

“Uh…” Reggie said. “Um, honestly, when I took this job I was promised that riddles weren’t actually a big part of it…”

“A date,” Edward said. “I want you to be my date tonight.” 

“Oh!” Reggie said. “Okay, that’s… sure. I accept.”

“Good,” Edward said. He handed Reggie a money clip, then said, “Here’s money to buy a nice suit. Meet me back here at 7.” 

 

 

Reggie arrived at the Riddler’s lair that night, wearing an expensive suit. He felt a rush as he walked past all his co-workers to knock directly on Edward’s door.

Edward opened the door and grinned. “You look absolutely dapper,” he said. He started pulling Reggie’s tie off.

“You don’t like the tie?” 

“I have a better one for you,” Edward said. He opened his desk drawer and took out a bright purple tie with green question marks all over it.

“Oh. Uh, that is better,” Reggie said politely. 

Edward started tying it around Reggie’s neck. “How tall are you?” When Reggie didn’t answer, he asked, “Did you not hear me?”

“Oh sorry,” Reggie said. “That sounded like one of your riddles so I was waiting for you to tell me the answer. I’m 6’2”.” 

Edward smiled and ran his hand down Reggie’s face. “I like that.” 

Reggie beamed proudly at him. 

 

Reggie followed Edward into the Iceberg Lounge. “I’ve never been in here when it wasn’t work-related,” he said. “Usually I just come in and rough up the Penguin’s henchmen until they give us a cut of the night’s profits.”

Edward grinned and asked, “And you always win?”

“Oh yeah, his henchmen are not that tough,” Reggie said. 

Edward happily wrapped his arm around Reggie and led him inside. “You wait here,” he told him. “You’re going to lure Oswald over to you. He’ll see the tie and he’ll see you and he’ll have to come over to you immediately.” He giggled with delight. 

“What do I do when he walks over to me?” Reggie asked, but Edward was already walking away.

 

It wasn’t long before Oswald got word of the attractive man in the Riddler tie. He walked over to him and looked him over. Reggie panicked and did the one thing he knew henchmen were supposed to do-- he punched Penguin.

As two of Oswald’s henchmen grabbed him, Edward rushed over.

“Can you please get your minions to take their paws off my date?” Edward asked.

Oswald looked at him with disbelief. “Date?”

“Yes,” Edward said, smirking. “He’s just my type. Blonde, great body…” he stepped close to Oswald so he could look down at him as he said, “Tall.” 

Oswald glared. “Well, your date punched me. You want to go to war, Nygma?”

“I didn’t tell him to do that,” Edward said. He grinned and added, “Although I did find it delightful.” 

When he saw one of Oswald’s henchmen take out a knife, Edward rolled his eyes and said, “I’m sorry that he punched you. I didn’t give him clear enough instructions. We don’t mean you any harm. I simply brought him here to enjoy a romantic evening. But, we can go if seeing us together would bother you.” 

Edward smirked at Oswald. Oswald stuck his nose up defiantly and asked, “Why would that bother me?” He turned to his lackeys and said, “Let go of him. If he wants to watch Ed attempt to dance all night, that’s his business.”

As soon as Reggie was released, Edward took his hand and led him onto the dance floor. He pulled him close, putting his hands tight on Reggie’s waist and grinding against his ass. 

 

At the end of the night, Edward led Reggie into his town car. He was about to ask him his address so he could drop him off when Reggie started kissing him. 

Edward pulled away and looked at Reggie with curiosity. He wasn’t sure why he didn’t seem to understand that his work was done.

Reggie looked back at him with an eager-to-please expression that Edward found really adorable. He ran his hand down Reggie’s back. 

“You’re really sexy,” he observed.

Reggie grinned and said, “Thanks. So are you. I mean, you’re definitely not my usual type, but there’s something… I don’t know… mysterious about you. It’s hot.” 

Edward smiled and kissed him. “Let’s go back to my place,” he said.

 

“You have a really nice house,” Reggie said, looking around the creepy gothic mansion as Edward led him up the stairs.

“Thank you,” Edward said, sliding his hand in Reggie’s back pocket. 

When they’d walked all the way down a hallway and reached a dead end, Reggie tilted his head with confusion. “You don’t have any doors.”

“Don’t I?” Edward aske with a little smile.

“No?”

“Will you hand me that red book on the top of that book shelf?” Edward asked him.

Reggie tried to pull on the red book and instead the shelf turned, revealing Edward’s bedroom.

“Dope!” Reggie said with a little smile as he walked in.

Edward wrinkled his nose. He put his hands on Reggie’s shoulders and asked him, “Say my name and I disappear. What am I?”

“Uh….”

Edward put a finger over Reggie’s mouth. “Silence.”

Reggie nodded and started taking his clothes off. Edward smiled.

“You’re a good henchman,” he said. 

Reggie smiled at him. When he was fully naked, he did a little spin. 

Edward put his hand under Reggie’s chin and kissed him, then pulled off his own clothes and got in bed. “I want you to suck my dick now,” he told him.

Reggie crawled over to him.

Edward grinned. He pet Reggie’s hair and said, “You know, you’re so uncomplicated it’s almost intriguing in its own way.”

“Thank you,” Reggie said. He put his hand over his mouth and said, “Whoops, sorry.”

“That’s alright,” Edward said. “You can talk a bit. But please don’t say ‘dope.’” 

“Oh, yeah, word,” Reggie said.

Edward sighed.

Reggie started gently sucking on his tip. Edward groaned and ran his hand through Reggie’s hair. 

Reggie started taking more in his mouth. Edward moaned and put a hand on the back of Reggie’s head, guiding it up and down. 

“Mmmmm,” Reggie said happily around Edward’s dick. 

He flicked his tongue over Edward’s tip a couple times before he went back to bobbing his head.

Edward pushed Reggie’s head away and came all over his chest. Edward pushed him down so that his head was resting on a pillow. “Stay like that so I can look at you until I fall asleep, then slip out,” he instructed.

“Cool,” Reggie said.

Edward watched him thoughtfully, then said, “I’d like to keep doing this. If you make yourself available whenever I need you, I’ll let you use my lair some weekends.”

“Uh… would I have to stop seeing other people?” Reggie asked. He felt a little terrified that Edward would get mad at him for even asking that. 

Edward wrinkled his nose. “I don’t care. Why would I? Just make sure you come quick whenever I need you. I’ll give you a pager to make it simple.”

“What will I say when it goes off around someone?” Reggie said.

“Just say you’re a doctor. You already have to lie to everyone about what your job is anyway, right?” 

Reggie grinned. “Good idea. You’re really, really smart.”

Edward laughed and messed up Reggie’s hair. “I know. Thank you.”


End file.
